Move slow.
Use lots and lots of lube.
Be completely relaxed and with a partner that you know you can trust 100%.
Don't tolerate any pain. Stop if it hurts.
Use gloves on hands and make sure nails are short.

If you're talking anal sex (or similar sized toys) as a goal then work up to it over as long as it takes. Plan on a couple of weeks, anyway, maybe even a couple of months. We (people in general) generally condition ourselves to "keep tight" down there, and it can take a while to learn how to relax.

Move slow. Use lots and lots of lube. Be completely relaxed and with a partner that you know you can trust 100%. Don't tolerate any pain. Stop if it hurts.Use gloves on hands and make sure nails are short.

If you're
...

Move slow. Use lots and lots of lube. Be completely relaxed and with a partner that you know you can trust 100%. Don't tolerate any pain. Stop if it hurts.Use gloves on hands and make sure nails are short.

If you're talking anal sex (or similar sized toys) as a goal then work up to it over as long as it takes. Plan on a couple of weeks, anyway, maybe even a couple of months. We (people in general) generally condition ourselves to "keep tight" down there, and it can take a while to learn how to relax.

My husband loves anal play and loves when I play with his prostate. He'd like for me to give it a try...but I'm a little leery and unfamiliar....any thoughts or tips?

I think the rule of thumb is to go with the flow. You can tell if your partner is enjoying the experience or if they are uncomfortable. Bringing them a new kind of pleasure can turn up the heat.

My husband and I started slow, with light touches, and licking. Once he got use to that we moved on to slow penetration with plenty of lube. Go small, and you can't go wrong. He'll guide you. Make sure to have open communication. I think that when couples are honest about their likes and dislikes, you can explore more together. And lets be honest, making them hot, makes us hot.